(1S,2S,3R,4R)-3-(2,3-Diamino-5-chloro-pyridin-4-ylamino)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide → HCID 178491968, compound

HRID 591945Notes

Reaction equation

HRID 591945 reaction equation
FC(F)(F)[C:3]([OH:5])=O.[Cl:8][C:9]1[C:10]([NH:31][C@@H:32]2[C@@H:37]3[CH2:38][C@@H:34]([CH:35]=[CH:36]3)[C@@H:33]2[C:39]([NH2:41])=[O:40])=[C:11]2[N:17]=[C:16]([C:18]3[CH:23]=[CH:22][C:21]([CH2:24][N:25]4[CH2:30]CO[CH2:27][CH2:26]4)=[CH:20][CH:19]=3)[NH:15][C:12]2=[N:13][CH:14]=1.N[C:43]1C(N)=C(N[C@@H]2[C@@H]3C[C@@H](C=C3)[C@@H]2C(N)=O)C(Cl)=[CH:45][N:44]=1>>[Cl:8][C:9]1[C:10]([NH:31][C@@H:32]2[C@@H:37]3[CH2:38][C@@H:34]([CH:35]=[CH:36]3)[C@@H:33]2[C:39]([NH2:41])=[O:40])=[C:11]2[N:17]=[C:16]([C:18]3[CH:23]=[CH:22][C:21]([CH2:24][N:25]4[CH2:26][CH2:27][N:44]([CH3:45])[CH2:43][CH2:30]4)=[CH:20][C:19]=3[O:5][CH3:3])[NH:15][C:12]2=[N:13][CH:14]=1

Participants

3

Reactant 2

HCID 117701912(1S,2S,3R,4R)-3-(2,3-Diamino-5-chloro-pyridin-4-ylamino)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amideHCID 178513995HCID 178513995, compound

Product 1

HCID 178491968HCID 178491968, compoundYield 18%

Procedure

In the same fashion as for Compound III, (1S,2S,3R,4R)-3-(2,3-Diamino-5-chloro-pyridin-4-ylamino)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide and 2-methoxy-4-(4-methyl-piperazin-1-ylmethyl)-benzaldehyde bis trifluoroacetate were reacted to produce the title compound (18%). 1H NMR (d-chloroform): 10.74 (s, 1H), 8.34 (d, J=7 Hz, 1H), 8.03 (s, 1H), 7.12 (m, 2H), 6.37 (m, 3H), 5.55 (d, J=8 Hz, 1H), 5.20 (t, J=7 Hz, 1H), 5.14 (br s, 1H), 4.08 (s, 3H), 3.58 (s, 2H), 3.18 (s, 1H), 2.91 (s, 1H), 2.88 (d, J=7 Hz, 1H), 2.52 (m, 4H), 2.36 (m, 1H), 2.33 (s, 3H), 1.74 (m, 4H), 1.29 (m, 1H). MS: 522.2 (M+H). HPLC retention time: 1.71 minutes (G Method).

Sources & evidence

ORD record
ord-2dd5690b347940c5b5a2d7a282465461
Source dataset
uspto-grants-2016_01
Patent number
US09238656B2

Reaction notes

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